Josh

1. Brandon Sullivan (Michael Fassbender), Shame
   
2. Richard Sherman (Tom Ewell), The Seven Year Itch
   
3. Jack (Thomas Haden Church), Sideways
   
4. Paul (Marlon Brando), Last Tango in Paris
   
5. Michelle Flaherty (Alyson Hannigan), American Pie

Michael Phillips

1. Lulu (Louise Brooks), Pandora's Box
   
2. Lily (Barbara Stanwyck), Baby Face
   
3. Sister Ruth (Kathleen Byron), Black Narcissus
   
4. Annie Laurie Starr (Peggy Cummins), Gun Crazy
   
5. Prof. Humbert Humbert (James Mason) and company, Lolita (1962)